4-(p-tolyl)chroman-2-one | 108679-56-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 4-(p-tolyl)chroman-2-one
• 英文别名: 3,4-Dihydro-4-(4-methylphenyl)-2H-1-Benzopyran-2-one；4-(4-methylphenyl)-3,4-dihydrochromen-2-one
• CAS: 108679-56-7
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: CLZHYDKPVFGXJU-UHFFFAOYSA-N

物化性质

• 沸点：
  352.7±37.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  水杨醛 在 1,2,3,4,5-pentacarbomethoxycyclopentadiene 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 12.0h， 生成 4-(p-tolyl)chroman-2-one
  参考文献：
  名称：

  有机布朗斯台德酸催化邻醌甲基化物与 1, 3-二羰基化合物的环加成反应：轻松获得呫吨酮和色满酮

  摘要：

  已经报道了在五羧基环戊二烯（一种有机布朗斯台德酸）存在下原位生成邻醌甲基化物及其逆电子需求 Diels-Alder 反应。已经完成了由醌甲基化物与 1, 3-二羰基和 Meldrum 酸的 [4 + 2] 环加成反应，以良好到极好的收率合成了呫吨酮和色满酮。这种方法的发展有助于产生许多具有药用价值的生物有效杂环。

  DOI：

  10.1002/jhet.4323

文献信息

• Microwave accelerated the solvent-free synthesis of 4-aryl-3,4-dihydrocoumarin via the tandem reaction of cinnamic acids with phenols catalyzed by Amberlyst 15 resin
  作者：Huu-Phuoc Le、Cong-Thang Duong、Xuan-Triet Nguyen、Thi Xuan Thi Luu

  DOI：10.1080/00397911.2021.1925918

  日期：2021.7.18

  Abstract Amberlyst 15 resin supported the tandem reaction of cinnamic acids with phenols under solvent-free reaction condition has been introduced to afford 4-aryl-3,4-dihydrocoumarin (neoflavanone) derivatives. The efficiency of solid acidic sulfonic resin (A-15) has been illustrated in two reaction activation methods such as microwave irradiation and conventional heating. The important roles of Amberlyst

  摘要 Amberlyst 15 树脂支持肉桂酸与酚类在无溶剂反应条件下的串联反应，得到 4-芳基-3,4-二氢香豆素（新黄烷酮）衍生物。固体酸性磺酸树脂 (A-15) 的效率已通过微波辐射和常规加热两种反应活化方法进行了说明。Amberlyst 15 的重要作用通过在微波辐射的辅助下比常规加热在更短的时间内产生高产率 4-芳基-3,4-二氢香豆素，以及其六次催化剂运行的高回收率和可重复使用性而得到强烈强调。通过XRD和FE-SEM对原始催化剂和回收催化剂进行表征，以研究再利用催化剂的表面与其可回收性的相关性。
• Palladium Catalyzed Enantioselective Hayashi–Miyaura Reaction for Pharmaceutically Important 4-Aryl-3,4-dihydrocoumarins
  作者：Jixing Lai、Chen Yang、René Csuk、Baoan Song、Shengkun Li

  DOI：10.1021/acs.orglett.1c04366

  日期：2022.2.18

  The first palladium-catalyzed asymmetric addition of arylboronic acids to coumarins was successfully established, providing a straightforward asymmetric approach to achieving pharmaceutically important 4-aryl-3,4-dihydrocoumarins. This methodology features easily accessible and bench-stable ligands, a wide substrate scope, mild conditions, and accommodation of electron-withdrawing arylboronic acids

  成功地建立了第一个钯催化的芳基硼酸不对称加成香豆素，为获得药学上重要的 4-aryl-3,4-dihydrocoumarins 提供了一种直接的不对称方法。该方法的特点是易于获得和稳定的配体、广泛的底物范围、温和的条件以及吸电子芳基硼酸的适应性。
• Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
  作者：Angélica M. Escobar、Diego M. Ruiz、Juan C. Autino、Gustavo P. Romanelli

  DOI：10.1007/s11164-015-2016-3

  日期：2015.12

  4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H14P5NaW30O110) (PA) as heterogeneous catalyst under solvent-free reaction conditions, at 130 °C, in a short reaction time (2 h). Under these conditions, very good yields (11 examples: 61 %–90 %), free of secondary products, were obtained. The catalyst is recyclable, nontoxic, neither air nor moisture sensitive, and easy to handle. The described methodology is a clean and useful alternative to synthesize oxygenated heterocycles based on a coumarin skeleton.

  在 130 ℃ 的无溶剂反应条件下，使用一种 Preyssler 结构的化合物 (H14P5NaW30O110) (PA) 作为异相催化剂，通过苯酚与苯丙炔酸和肉桂酸的直接酯化反应，分别制备了 4-苯基和 3,4-二氢-4-苯基香豆素，反应时间短（2 h）。在这些条件下，获得了非常好的产率（11 个实例：61 %-90 %），且无二次产物。该催化剂可回收、无毒、对空气和湿气都不敏感，并且易于处理。所述方法是合成基于香豆素骨架的含氧杂环的一种清洁而有用的替代方法。
• Rhodium-Catalyzed Domino Conjugate Addition−Cyclization Reactions for the Synthesis of a Variety of <i>N</i>- and <i>O</i>-Heterocycles: Arylboroxines as Effective Carbon Nucleophiles
  作者：Ja Ock Park、So Won Youn

  DOI：10.1021/ol100610v

  日期：2010.5.21

  Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.
• Organic Brønsted acid‐catalyzed cycloadditions of<scp><i>o</i>‐quinone</scp>methides with 1,<scp>3‐dicarbonlys</scp>: Facile access to xanthenones and chromanones
  作者：Priyadarshini Thoppe Sivakumar、Sharathna Puthiyaparambath、Sanjay Suresh Varma、Sasikumar Parameswaran、Radhakrishnan Kokkuvayil Vasu

  DOI：10.1002/jhet.4323

  日期：2021.10

  The in-situ generation of o-quinone methides and their inverse-electron-demand Diels–Alder reaction in the presence of pentacarboxycyclopentadiene—an organic Brønsted acid—has been reported. The synthesis of xanthenones and chromanones in good to excellent yields from the [4 + 2] cycloaddition of quinone methides with 1, 3-dicarbonyls and Meldrum's acid has been accomplished. The development of this

  已经报道了在五羧基环戊二烯（一种有机布朗斯台德酸）存在下原位生成邻醌甲基化物及其逆电子需求 Diels-Alder 反应。已经完成了由醌甲基化物与 1, 3-二羰基和 Meldrum 酸的 [4 + 2] 环加成反应，以良好到极好的收率合成了呫吨酮和色满酮。这种方法的发展有助于产生许多具有药用价值的生物有效杂环。